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Seven basic steps for gay anal sex without any pain:
1.) Clean out your ass (to avoid a mess and skin abrasions)
2.) Turn-on with foreplay (cuddle, kiss, get hard, jerk off, suck, etc.)
3.) Rim job (ass licking)
4.) Lube and finger your ass (to relax the asshole muscle)
5.) Dildo fuck your ass (to stretch it and lube it inside)
6.) Put on a condom (to prevent sexually transmitted infections)
7.) Fuck and cum (without any pain)
I did not learn anything about gay anal sex until my freshman year in
college. When I first heard about it, I wondered how anybody could
enjoy being fucked in the ass. As an enthusiastic cocksucker, it was
easy to ignore anal sex until the first time I watched a porno video of
two gay guys fucking. I was surprised that the sight of gay ass fucking
made me so horny and interested in losing my anal virginity. I needed
no further explanation the first time my cock, without being touched,
started shooting cum when a hard dick was shoved up my ass.
My high school sex education classes taught me nothing about gay sex,
except that condoms must be used to prevent AIDS. A simple Google
search for more information only provided me with many safe sex and
porno web pages. Safe sex is important, but since information about it
is easily available elsewhere I will avoid repeating most of it here.
However, good instructions on how to ass fuck are much harder to find.
For this reason, I describe below how to enjoy being fucked in the ass
without any pain. Perhaps reading this will spare you from repeating
the mistakes I made. Of course, what works for me may not work for you
because everybody is different. But don't give up too soon since most
people require lots of practice.
Also, before giving up, check out the list of good web page links and
books at the end of this page. The links are current as of Jan. 2006.
If they are rotten by the time you read this, you might be able to find
equivalent pages with a Google search.
One of the biggest fears of gay virgins is that a dick will be too big
to fit in their ass. For example, the following note was posted on the
Internet by a 21-year-old senior at Penn State University:
"So my friend and I made it back from the club the other night and
started going at it pretty hot and heavy. We got down to nothing pretty
quickly, then between the panting and the grunting agreed to fuck each
other--except, neither one of us had ever done it before. We whipped
out the condoms, put them on, and tried to have a go at it (in the
dark). Maybe we're fucking stupid or something (no pun intended) but we
couldn't do it. I think we are both too tight, but I'm not sure.
Neither one of us could seem to get it into the other. We both wear
Lifestyles large condoms, is there a chance we could be *too* big for
penetration? I sincerely doubt that, I mean, we're not that big. I
asked him and confirmed that neither one of us has ever had so much as
a finger up our asses. Does anyone have any advice for first-timers?" (Quoted from www.billyspervwebsite.com)
I remember having the above concern when I was an anal virgin. The
first time I played with a dildo, I recall thinking that it would never
go inside. But with lots of lube, along with slow and steady pressure,
the dildo popped through my anal ring just before I was about to give
up. Unfortunately, the resulting flash of pain made me to pull it out
too quickly, which only caused even more pain. Sure, it fit, but I was
still left wondering if a dick could ever fit inside of me without any
I went searching for answers and learned that it is normal for asshole
muscles to clamp tight when pushed from the outside. Experienced
bottoms (guys who like being fucked in the ass) told me that even the
biggest dick will fit provided the asshole muscle has been properly
relaxed and slowly stretched open. But nobody could tell me exactly how
to do this.
One gay buddy reminded me that my asshole regularly passed shits that
were bigger than most dicks. To him, this was proof that a dick would
fit in my asshole. Apparently, special nerves allow shit to
automatically and painlessly open up the asshole. The trick to painless
butt fucking is learning how to relax your asshole muscles just as you
do when you take a shit. Unfortunately, few anal virgins are able to do
this naturally without any practice.
It is best to practice alone first, without a partner. That way you can
relax, go at your own pace and not have to worry about pleasing a
partner. Anal play will also toughen the skin around your asshole,
which will prevent painful abrasions when you finally get fucked. You
can easily practice most of the seven steps described below without a
It took me several years before I was able to relax with a partner and
not worry about any pain on entry. Now, I seem to have voluntary
control over my asshole muscles, especially when I am horny and begging
to be fucked. And even when I experienced pain on initial entry, I
still enjoyed being fucked because the pain would go away quickly if my
partner held still for a moment or pulled out slowly and slowly
reentered after the pain had subsided.
After you are able to fuck yourself with a dildo without any pain, be
sure to find a partner that is willing to do the following seven steps
at your speed. Many tops (guys who like to fuck ass) often want to fuck
ass immediately and they are used to experienced bottoms that are able
to take it. Make sure your partner knows in advance that you are
inexperienced and will need him to go more slowly. If your partner is
versatile (likes fucking and being fucked), try fucking him to learn
how it works. Remember, practice makes perfect.
1.) CLEAN OUT YOUR ASS
In addition to worrying about a dick being too big for painless
fucking, gay bottoms frequently worry about being "clean down there."
Not only is it embarrassing to see shit on a top's dick when he pulls
out, but shit is very abrasive, which can make fucking very
Often, the only thing you will need to do before sex is to wash the
outside of the asshole to eliminate any foul odors or tastes. This will
be sufficient only if your shits have come out cleanly without leaving
anything behind. For many guys, this happens naturally when they eat a
healthy low-fat, high-fiber diet and avoid liquor and caffeinated
drinks, such as Coke and coffee. Of course, everybody is different and
so you will need to experiment with different diets to find one that
The best way to determine if you are clean is the "finger test." This
is done by inserting a lubed finger in your ass while sitting over a
toilet. If you feel any small pieces of shit, you can gently pull them
out. Doing this will also pre-lube your ass. Of course, be sure to wash
your hands and butt before having sex.
However, if your finger feels messy soft shit inside your ass, you can
try washing it out with an enema or douche. Unfortunately, enemas can
make things messier because water will often get trapped inside and
come gushing out unexpectedly during sex. This is why you should always
do anal play over a towel that can be easily laundered. It is also a
good idea to have a roll of paper towels and baby wipes nearby to clean
up any messes that might occur.
According to some doctors, enemas may harm you and so they should be
used sparingly, if at all. Disposable enema bottles can be easily
purchased in most drug stores. The Fleet brand is commonly available in
the U.S.A. They come pre-filled with harsh chemicals that can give you
cramps during sex. To avoid any problems, I will pour the chemicals out
and refill the bottle with clean water. Be sure to use bottled water if
your tap water is unsafe to drink.
Another alternative is to use the small rubber bulb that comes with ear
wax removal kits. It will hold a smaller amount of water, which makes
it less likely that water will get trapped inside your ass.
After filling the enema bottle or rubber bulb with clean water, lube
the tip and gently insert it in your ass. Slowly squeeze the bottle to
squirt water inside. Pull the tip out before letting go to prevent
water from being sucked back into the bottle. Hold the water inside for
awhile before dumping it in the toilet. You may need to do this several
times until the water runs clean.
A cleaning technique I use is to stick a lubed finger in and swish the
enema water around to remove any shit stuck to the sides. The pieces
knocked off will then easily come out when you dump the water. I repeat
as needed and wash my hands and butt to finish cleaning up.
Guys who are heavy into anal play, such as fisting, often use shower
attachments that can be stuck up the butt to provide a pressure wash.
They do a good job of cleaning, but when used incorrectly they can
cause bleeding, which might require an embarrassing ambulance ride to
the hospital emergency room.
2.) TURN-ON WITH FOREPLAY
Foreplay will help you turn-on sexually, which will relax your asshole
and make it receptive to being fucked. Cuddling, kissing, jerking off,
and sucking dick are some of the ways to get sexually excited and ready
to be fucked.
The area around the asshole will become puffy and engorged with blood
as you become more sexually excited. Experienced ass fuckers can often
feel their asshole lips spread open and beg to get fucked. Inadequate
foreplay is probably the number one cause of painful anal intercourse.
3.) RIM JOB
A rim job is when your partner licks around your asshole and gently
fucks it with his tongue. When practicing by yourself, you can simulate
rimming by rubbing a spit covered finger around the outside of your
asshole. Try jerking off while your finger tip gently spreads the
asshole open. Experiment with different methods to see what feels good.
When you are ready to play with a fuck buddy, have him lick around the
rim of your asshole. Make sure he uses a lot of spit so that his tongue
can slide and press gently into your asshole. Jerk off and feel your
asshole muscles relax and spread open. When he starts to tongue fuck
your asshole, it will not be long before you are begging him to fuck
Licking ass can spread hepatitis and other diseases. Your doctor can
give you a shot to avoid hepatitis. Dental dams can be used for safety,
but they tend to be impractical.
4.) LUBE AND FINGER YOUR ASS
Even though a good rim job will make you desperate to be fucked, you
should slow down and enjoy some fingering first. Fingering is also
something you should first practice by yourself without a partner.
A single finger should be lubed and slowly pressed into the asshole.
Spit is good enough for tonguing and fingering the outside of the
asshole, but spit does not provide enough lube for insertion unless
your asshole is very experienced.
The best lubes are tasteless and water soluble for easy clean up. KY
Jelly is a common brand of water soluble lube sold in America. Have fun
and try out different brands to find one you like.
Oil based lubes are more slippery and last longer than water soluble
lubes, but they can damage latex rubber condoms. Many products, such as
some versions of Vaseline-brand petroleum jelly, can also contain other
chemicals, which will irritate your asshole skin.
Start with the tip of a lubed finger gently spreading the ass lips
apart. Use a slow and steady, in and out motion, so that the finger
goes in a little bit deeper and deeper each time. Don't rush and go too
fast or it will hurt. If it hurts, slowly pull the finger out and let
the asshole muscles calm down. Sometimes wiggling the finger will help
it slide further into the asshole. At some point, the finger will snap
past the asshole ring and pop into the looser rectum. When this
happens, stop and hold still to let the asshole muscles get used to the
Try jerking off with a finger up your ass to discover what feels good.
Just before you cum, you should be able to feel the prostate gland
because it will get really hard. Some guys will cum just from their
prostate being stroked without even touching their dick. Experiment
with different angles and pressure to find out how your prostate likes
to be stroked.
After you are able to take one finger without pain, try slowly working
in two and then three fingers and fuck yourself with them. It will
probably take multiple practice sessions to achieve three fingers
without experiencing any pain. Remember that you can never have too
When a partner is fingering you, be sure to let him know what feels
good or bad. He can only adjust the pressure and angle of his fingers
based on your feedback. If he gets you worked up with three fingers,
you will be more than ready to try being fucked.
For safety, make sure the fingernails are cut and filed to prevent any cuts. Surgical gloves can also be used.
5.) DILDO FUCK YOUR ASS
Even though being fucked by three fingers will probably make you more
than ready to be fucked by a dick, using a dildo first can be helpful.
Fucking yourself with a dildo is also a good way to practice on your
own while jerking off.
A partner can insert a lubed dildo to prepare your ass for fucking. But
I like to insert it myself because I can control the angle and pressure
to make insertion pain free. Once the dildo is inside and my asshole
muscles are relaxed, I will let my partner fuck me with it. It is also
fun to let a partner fuck you with a dildo while he sucks your dick.
Playing with dildos is a great way to learn how to be fucked without
pain. It will also toughen up the skin around your asshole so that you
are less likely to get skin abrasions during fucking. When you have
mastered dildos, a real dick will easily slide in without any pain.
Another benefit of using a dildo before fucking is that you will know
if you are "clean" inside. Likewise, a condom placed over the dildo
makes for easy clean up afterward. Bacteria can grow in the dildo
material. For safety, do not share dildos unless you cover them up with
a new condom.
The only problem with the dildos sold in most stores is that they are
much too big. Make sure you buy a dildo that is less than 5 inches
around (that is about one and a half inches across) and less than 7
inches long. The bigger dildos are too hard to use unless you are very
Small dildos are very hard to find, but they can be purchased online. A
group of San Francisco lesbian feminists make and sell some very good
small dildos. (As of January, 2006, some of their dildos that are small
include: www.goodvibes.com Acute Ambrosia (5 1/4 long, 1 1/4 in diameter) for $36.00 and www.goodvibes.com Leo Black (7 1/4 long, 1 1/2 in diameter) for $50.00 )
Dildos made from silicone rubber, such as the ones mentioned above, are
very expensive, but they are easy to clean and well worth the price.
Be careful using improvised homemade dildos. They can break, get lost
inside and damage your rectum, which might require a trip to the
hospital emergency room.
6.) PUT ON A CONDOM
When you are both ready, have your partner roll on a condom over his
hard dick and lube it up well. It is better to have too much lube for
fucking than too little. The prior fingering and dildo play you did
should have your ass well lubed and ready to be fucked.
Bareback sex without a condom is fun, but it is not worth the risk of
death from AIDS. Only partners who have both tested HIV-negative should
risk having bareback sex. And both partners must completely trust that
their partner will not secretly fool around on the side and acquire HIV
after being tested. Besides, bareback sex exposes you to other sexually
transmitted infections that can be expensive to treat.
7.) FUCK AND CUM
If you and your partner have done all of the previous steps, you will
be good and ready to be fucked by a real dick. Don't rush things. You
should practice the previous steps over several weeks, both by yourself
and with your partner, to get some experience.
Several hours of foreplay, fingering and dildo action may be necessary
for a painless fuck. You should be so excited that you cum in less than
ten minutes during the actual fucking part.
There are many possible positions for anal sex. The squatting position
is a good one for anal beginners because it allows them to control how
fast the dick slides in their ass. In this position, the top lies on
his back and the bottom squats over his hard dick. The bottom then
slowly squats down letting his asshole slide down his partner's dick.
When the asshole muscle has relaxed, you can move to other fucking
/\ o /\
/ \_/^\_/ \
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ASCII TEXT PICTURE
OF A SQUAT FUCK
Other guys find doggy style (kneeling on all fours) more comfortable.
The missionary position (being fucked while reclining back with your
legs spread apart and up in the air) is also popular because it is
relaxing and allows both partners to see each other.
No matter which position you choose, give your partner access to your
asshole by spreading your butt cheeks. Let him gently press the tip of
his dick against your asshole. Add lube as needed. Each time he presses
against your asshole, it will slowly spread open wider and wider. You
will probably feel your asshole muscles resisting his entry. Do not
panic because with slow and steady pressure, your asshole will
eventually relax and open up.
At some point your partner will press so hard that the tip of his dick
will all of a sudden pop inside your asshole. This will probably take
away your breath and it might hurt a little bit. Ask your partner to
stop and hold still until the pain goes away. If necessary, have him
slowly withdraw and wait for any muscle spasms to go away. His dick
will go in much easier the next time.
Some guys like to have the dick shoved in all at once and then wait for
the pain to subside. This seems risky to me because it can tear the
asshole skin and cause bleeding.
I prefer having the dick slowly pushed in and out with it going a
little bit deeper on each stroke. It takes several minutes to get the
dick completely inside me, but I can avoid any pain with this method.
Besides, I find a slow insertion to be very erotic.
After your partner has completely buried his dick in your ass, he
should remain motionless for awhile to allow your asshole muscle to
relax. When any pain has subsided, he should start slowly fucking in
and out. Be sure to experiment and see what feels good. Have him adjust
the angle and speed of his thrusting if anything hurts. Before long,
you will be begging him to fuck you faster and harder. You will feel no
pain, just pleasure.
Also, be sure to jerk off while you are being fucked. The pleasurable
sensations of fucking will send you out of this world. When you cum,
your asshole muscles will contract around your partner's dick, which
may cause him to cum too. Some guys love to pull out, take off the
condom and cum all over your ass, chest or face like in a porno video.
If you cum inside, be sure to hold the top of the condom as you pull
out so that it does not get stuck inside.
With a little bit of practice you will enjoy being fucked in the ass so
much that you will not be able to get enough of it. Unless your
boyfriend is a total top, the two of you will want to trade off so that
you both get your share of being fucked. It is boring to limit yourself
to be a top or a bottom only. Being able to both fuck and be fucked in
the ass is truly one of the unique joys of gay sex.
SOME GOOD BOOKS AND WEB LINKS ABOUT ANAL SEX:
A book by Jack Morin, PhD, "Anal Pleasure & Health,"
was first published in 1981, with a second edition in 1986, and third
edition in 1998. This was the first book to do a good job of addressing
A speech by Jack Morin, PhD, "Ten Rules of Anal Sex," can be read at www.sexuality.org/authors/morin/analrule.html
A book by Bill Brent, "The Ultimate Guide to Anal Sex for Men," is also good.
"The Joy of Gay Sex"
book covers more than just anal sex and it was fully revised and
expanded in a 2003 3rd edition by Dr. Charles Silverstein and Felice
Pecano. It includes many sexy illustrations of gay sex. This is the
granddaddy of gay advice books. The first edition was published in 1977 and was written by Dr. Charles Silverstein and Edmund White. The 1992 edition was titled "The New Joy of Gay Sex"
and was written by Dr. Charles Silverstein and Felice Picano with a
preface by Edmund White. Used copies of the previous editions are
sometimes hard to find on the used market, but they are interesting to
read to see what has changed over time. Check out the "First Time"
section on pp. 91-95, "Anus" p. 1, "Bottom" p. 22, "Bottoms Up" p. 24,
"Lubricants" p. 154, "Rear Entry" p. 208, "Relaxation" p. 211, "Rimming
and Felching" p. 212, "Safe Sex" p. 218, "Sex Toys" p. 235, "Side by
Side" p. 256, "Sit on My Face" p. 256, "Sitting on It" p. 260, "Top" p.
282, "Versatility" p. 301, and other sections.
A book by Dan Savage, "Savage Love: Straight Answers from America's Most Popular Sex Columnist," includes gay sex advice. Savage is the very funny sex advice columnist for the Seattle alternative weekly newspaper thestranger.com
Also, checkout Tristan Taormino's anal advisor (for all sexual persuasions) at www.puckerup.com
Finally, a British AIDS organization publishes the wonderful "F:S
Magazine" to educate young gay men about sex. The Adobe Acrobat PDF
versions are worth downloading from www.metromate.org.uk/fs/index.phtml (FS Magazine was originally called "Fuck Sheet")
A GOOD BOOK AND WEB SITE FOR GAY MEDICAL ADVICE:
A book by the gay Dr. Stephen E. Goldstone, M.D., "The Ins and Outs of Gay Sex," provides excellent medical advice.
Dr. Stephen E. Goldstone, M.D. also runs the web site www.gayhealth.com that included the following web pages as of Jan. 2006 (be sure to check for any page updates):
Sample gayhealth.com news posting: STUDY: 14% of MSM Intentionally Have Unprotected Anal Sex Friday, April 5th 2002
Sample gayhealth.com forum posting:
"RE: Can't orgasm from anal sex! (18 April 2001 GayHealth: Ask the
Doctors) by: anonymous 05/13/2001 @ 12:53AM Dr. Goldstone's answer to
the 18 April 2001 question "Can't orgasm from anal sex" asked for
advice on how to ejaculate without masturbating while being fucked. I
can vouch from first hand experience that "no-handed cumming" is not
just a favorite fantasy of gay porno writers.